Branched-chain sugars represent a rare class of naturally occurring carbohydrates. Such derivatives often show unique structural characteristics that are associated with notable biolological activity.1-2 A new type of rearrangement is described for preparation of 3-C-branched chain aldoses.3 The studied transformation is based on the Mo(VI)-catalyzed isomerization of carbohydrate carbon skeleton and allows preparation of C-3 isomers of 3-C-branched aldoses in a simple way without formation of side products. This rearrangement at C-3 carbon differs from the previously described epimerization at C-2 of aldoses catalyzed by Mo(VI) ions, known as Bílik reaction. The potential of this new transformation is illustrated on the preparation of new, 3-C-methyl-D-glucose and 3-C-vinyl-D-glucose from 3-C-methyl-D-allose and 3-C-vinyl-D-allose, respectively.
References
1. Yoshimura, J. Adv. Carbohydr. Chem. Biochem. 1984, 42, 69-134.
2. Kochetkov, N. K. Russ. Chem. Rev. 1996, 65, 735-768.
3. Hricovíniová, Z., Hricovíni, M. Carbohydr. Res. 2013, 370, 1-8.
